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Home > Encyclopedia > trans-Cinnamyl alcohol

trans-Cinnamyl alcohol

trans-Cinnamyl alcohol structure

trans-Cinnamyl alcohol 

structure
  • CAS No:

    4407-36-7

  • Formula:

    C9H10O

  • Chemical Name:

    trans-Cinnamyl alcohol

  • Synonyms:

    2-Propen-1-ol,3-phenyl-,(2E)-;Cinnamyl alcohol,(E)-;2-Propen-1-ol,3-phenyl-,(E)-;(2E)-3-Phenyl-2-propen-1-ol;trans-Cinnamyl alcohol;1-Phenyl-1-(E)-propen-3-ol;(E)-Cinnamyl alcohol;trans-3-Phenyl-2-propen-1-ol;(E)-3-Phenyl-2-propen-1-ol;(E)-3-Phenyl-2-propenol;trans-Cinnamic alcohol;trans-3-Phenyl-2-propenol;(E)-Cinnamic alcohol;trans-1-Phenyl-1-propen-3-ol;trans-3-Phenyl-2-propenyl alcohol;(2E)-3-Phenylprop-2-en-1-ol;1613504-07-6

  • Categories:

    Natural Products  >  Phenylpropanoids

Description

Solid


3-Phenylprop-2-en-1-ol is a reactant in the preparation of isobenzofuranones.


Liquid|Solid|White to yellowish crystalline solid, warm-balsamic, floral, sweet odour


Cinnamyl alcohol is a primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified). It has a role as a plant metabolite.|Cinnamyl alcohol is a naturally occurring compound that is found within cinnamon. Due to the low levels found in cinnamon, cinnamyl alcohol is usually supplied as [DB14184] within commercial products. Cinnamyl alcohol has been shown to be a skin sensitizer, with a NOEL (No Effect Level) of ~4%. Sensitivity to cinnamyl alcohol may be identified with a clinical patch test.|Cinnamyl alcohol is a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is by means of Increased Histamine Release, and Cell-mediated Immunity.

trans-Cinnamyl alcohol Basic Attributes

134

134.18

203-212-3

SS8YOP444F

623440|8775

DTXSID9041491

NEEDLES OR CRYSTAL MASS|WHITE TO YELLOWISH SOLID|WHITE NEEDLES FROM PETROLEUM ETHER

2906299090

Characteristics

20.2

1.9

1.0442 g/cm3 @ Temp: 20 °C

32 °C

248-252 °C

126 DEG C

1.599

FREELY SOL IN ALC, ETHER, OTHER COMMON ORGANIC SOLVENTS; SOL IN WATER, GLYCEROL; CLEARLY SOL IN 3 VOL 50% ALC

0.02 mmHg

ODOR OF HYACINTH|PLEASANT, FLORAL ODOR

BITTER TASTE

MIN CONGEALING POINTS SPECIFIED BY ESSENTIAL OIL ASSN: 33.0 °C FOR PURE; 28.0 °C FOR ALC PRISM; 20.0 °C FOR CINNAMIC ALC FROM STORAX|ALDEHYDE CONTENT: NOT MORE THAN 1.5% (AS CINNAMIC ALDEHYDE)|UV: 74 (Sadtler Research Laboratories Spectral Collection) /Cinnamyl alcohol (cis)/

Safety Information

GE2200000

IS OXIDIZED SLOWLY ON EXPOSURE TO HEAT, LIGHT, & AIR

P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, P501

H302

121.1164

|Warning|H317 (97.95%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 1908 companies from 22 notifications to the ECHA C&L Inventory.|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P333+P313, P337+P313, P363, and P501|Aggregated GHS information provided by 7 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Drug Information

Cinnamyl alcohol is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

Cinnamyl alcohol is 66% absorbed through the skin and shown to be rapidly absorbed from the gut.|Cinnamyl alcohol is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 76–77% of the dose of cinnamyl alcohol was recovered in the urine and feces within 24 h.|CINNAMYL ALC IS EXCRETED UNCHANGED IN NEUTRAL EXTRACT WHEN GIVEN TO RATS.

In general, esters containing an aromatic ring system are expected to be hydrolyzed in vivo. Cinnamyl alcohol is hydrolyzed to [DB14184].|ACIDIC & NEUTRAL URINARY METABOLITE OF CINNAMYL ALC WAS IDENTIFIED THROUGH A COMMON METABOLIC SCHEME.|Cinnamyl alcohol is a known human metabolite of beta-methylstyrene.

PATCH TESTS TO SEVERAL SCREENING SETS OF FRAGRANCE MATERIALS WERE PERFORMED ON 20 PERFUME-SENSITIVE PT. MOST COMMON ALLERGEN WAS CINNAMIC ALC (15 OF 20 PT).

3-phenyl-2-propene-1-ol

trans-Cinnamyl alcohol Use and Manufacturing

Methods of Manufacturing

MEERWEIN-PONNDORF REDUCTION OF CINNAMALDEHYDE WITH ALUMINUM ISOPROPYLATE OR ETHYLATE; ALKALINE HYDROLYSIS OF STORAX; REDUCTION OF CINNAMAL DIACETATE WITH ACETIC ACID AND IRON FILINGS|OBTAINED ORIGINALLY BY SAPONIFICATION OF CINNAMYL CINNAMATE (STYRACIN). THIS METHOD OF EXTRACTION FROM STORAX IS STILL USABLE. SYNTHETICALLY, BY REDUCTION OF CINNAMALDEHYDE WITH SODIUM OR POTASSIUM HYDROXIDE.

Uses

Flavor and Fragrance


Air care products

Production

100,000 - 500,000 lb|(1974) 6.81X10+7 G-CONSUMPTION IN FRAGRANCES|(1979) PROBABLY GREATER THAN 9.08X10+5 GRAMS

ASSAY: 98% MIN

All other basic organic chemical manufacturing|2-Propen-1-ol, 3-phenyl-: ACTIVE|WHEN SMALL AMT OF IMPURITIES ARE PRESENT AS IN NATURAL ARTICLE (CINNAMYL ALC FROM STORAX), IT REMAINS FLUID AT LOWER TEMPERATURES THAN THE MELTING POINT.|REPORTED USES: NON-ALCOHOLIC BEVERAGES 8.8 PPM; ALCOHOLIC BEVERAGES 5.0 PPM; ICE CREAM, ICES, ETC 8.7 PPM; CANDY 17 PPM; BAKED GOODS 33 PPM; GELATINS & PUDDINGS 22 PPM; CHEWING GUM 720 PPM.|FLAVOR USEFUL IN APRICOT, PEACH, RASPBERRY, PLUM FLAVORS.|OCCURS (IN ESTERIFIED FORM) IN STORAX & IN BALSAM PERU, CINNAMON LEAVES, HYACINTH OIL. OBTAINED BY ALKALINE HYDROLYSIS OF STORAX.|For more General Manufacturing Information (Complete) data for 3-PHENYL-2-PROPEN-1-OL (6 total), please visit the HSDB record page.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking

Flavoring Agents

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, custom temperature program Capillary DB-5MS 1302. custom temperature program 30. m/0.25 mm/0.25 μm, He; Program: 40C => 2C/min => 60C => 4C/min => 260C Maia, J.G.S.Andrade, E.H.A.Zoghbi, M.G.B.Volatile constituents of the leaves, fruits and flowers of cashew ( Anacardium occidentaleL.)J. Food Comp. Anal.2000, 13, 3, 227-232.
Kovats' RI, non-polar column, custom temperature program Capillary Supelcowax-10 2334. temperature ramp He, 35. C @ 5. min, 3. K/min, 200. C @ 20. min; Column length: 60. m; Column diameter: 0.25 mm Wong, K.C.Teng, Y.E.Volatile Components of Mimusops elengi L. FlowersJ. Essent. Oil Res.1994, 6, 5, 453-458.
Kovats' RI, non-polar column, custom temperature program Capillary DB-1 1278. temperature ramp 25. m/0.2 mm/0.33 μm, 4. K/min; Tstart: 50. C; Tend: 300. C Osorio, C.Alarcon, M.Moreno, C.Bonilla, A.Barrios, J.Garzon, C.Duque, C.Characterization of Odor-Active Volatiles in Champa ( Campomanesia lineatifolia R. P.)J. Agric. Food Chem.2006, 54, 2, 509-516.
Kovats' RI, non-polar column, custom temperature program Capillary HP-5MS 1310.1 custom temperature program 30. m/0.25 mm/0.25 μm, He; Program: 60C (1 min) => 5 C/min => 210C => 10 C/min => 280C (15 min) Andriamaharavo, N.R.Retention Data. NIST Mass Spectrometry Data Center.NIST Mass Spectrometry Data Center, 2014.
Kovats' RI, non-polar column, custom temperature program Capillary DB-5 1303. custom temperature program 30. m/0.25 mm/0.25 μm, He; Program: 40C(2min) => 4C/min => 220C => 20C/min => 280C Andrade, M.S.Sampaio, T.S.Nogueira, P.C.L.Ribeiro, A.S.Bittrich, V.Amaral, M.C.E.Volatile compounds of the leaves, flowers and fruits of Kielmeyera rugosa Choisy (Clusiaceae)Flavour Fragr. J.2007, 22, 1, 49-52.

Computed Properties

Molecular Weight:134.17
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:134.073164938
Monoisotopic Mass:134.073164938
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:101
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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